Top 20 Fashion Icons--From Marilyn to Madonna And More!

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From Grace Kelly’s refined aesthetic to Madonna’s rebellious sensibilities, these icons leave us with an unforgettable sartorial legacy, inspiring women then and now to replicate their look. Click through our slideshow to see who made the cut.

Jean Seberg

Although Seberg was actually from small-town Iowa, the actress’ penchant for Breton stripe t-shirts, crisp blouses, and slim trousers came to personify everything cool and sophisticated about Parisian style.

Jacqueline Kennedy Onassis

The former First Wife was the picture of classic, all-American polish. Even after she remarried to Greek tycoon Aristotle Onassis, shifting her style from pillbox hats and shift dresses to oversized sunglasses and head scarves, the public continued to remain fascinated by her look.

Jane Birkin

Hermes’ renowned Birkin bag is named after the British actress, who captured a free-spirited, bohemian-inspired style in the ‘60s--think: slightly sheer blouses, micro shorts, and flared jeans--that felt decidedly French.

Diana Ross

The word “fierce” is part of Beyonce vernacular now, but back in the ‘60s, it belonged solely to Ross. The Supremes singer’s name is synonymous with glitz and glamour, thanks to her bedazzled outfits, bigger-is-better jewels, and voluminous coiff.

Faye Dunaway

We can’t think about Dunaway without envisioning the actress’ signature beret hats, short-sleeve sweaters, and midi skirts, the elegantly appealing look she sported in 1967’s Bonnie and Clyde and also off the clock.

Bianca Jagger

Often spotted in turbans, sequined pieces, and truly fabulous hats, Jagger was fashion-forward even for her time. The model--and Studio 54 fixture--embraced the bold, flashy outfits that cemented her fashion icon status.

Anita Pallenberg

As the paramour of more than one member of the Rolling Stones in the swinging ‘60s, it’s only fitting that Pallenberg commandeered a rock ‘n’ roll sense of style: swingy mini dresses, wide-brimmed hats, fringed vests, and kohl-rimmed eyes.

Lauren Hutton

Hutton’s approach to dressing is best described as effortlessly natural, much like the gap-toothed smile that became her beloved trademark. The actress and supermodel wore button-downs, slouchy pants, and simple t-shirts with an enviable laissez-faire attitude.

Diane Keaton

Who could forget Keaton dressed in a vest, tie, and bowler hat in her famous role as Annie Hall? The actress’ borrowed-from-the-boys style revolutionized the way women dressed in the late ‘70s and early ‘80s--and we’re thankful for it!

Madonna

Madonna has continued to reinvent her look over the decades, but it’s the Material Girl’s first appearance on the scene--wearing conical bras and studded bustiers in the ‘80s--that make her a fashion trailblazer.